Wittig Reaction Lab Report

The Wittig reaction is valuable reaction. It has unique properties that allows for a carbon=carbon double bond to form from where a C=O double bond used to be located. Creating additional C=C double bonds is valuable due to its use in synthesis. The Wittig reaction will allow the synthesis of Stilbene (E and Z) from a Benzaldehyde (Ketcha, 141).
One purpose of a Wittig reaction is the formation of alkenes from aldehydes or ketones employing a carbo-phosphorous ylide, which is stabilized vie resonance to allow for the carbon bonded to phosphorus to be deprotonate from by a base (Ketcha, 142). The resonating ylide will react with the electrophilic carbonyl carbon of its aromatic aldehyde to produce a betaine intermediate, or a crystalized 4

The percent yield was 22.33%. In most cases, that means that a lot of possible product was lost. However, in this case, that was not true. When Benzaldehyde reacted with the Wittig reagent, it produced two products: E-Stilbene and Z-Stilbene. The Z product was a liquid, while the E product was a solid. The final product weight for percent yield was only the solid E product, which missed one half of the final product produce. If both products were weight, the percent yield would have been larger that it was. Instead of 22.33%, it could have been 44.66%.
To prove that both products were obtained, but only one of the two products was analyze, a TLC plate of the DCM layer, that contains both products, and of the final product, was obtain. Both had a single dot at Rf value of 0.924. However, the DCM layer dot was double in intensity than the final product. This means that there was more product in the DCM layer than there was in the final

This was proved by utilizing the IR spectrum to verify the C=O was not in the final product as it lacked the 1640 cm-1 peak. The melting point of 113-115 degrees C proved that the final product obtained was the E-Stilbene. The TLC plate proved that the E and the Z product was produced, show cased by the double intensity of the DCM spot to the final product’s spot, both which had an Rf of 0.92. The double intensity proved that both products were produced, but through heating and filtering, the Z-Stilbene was